4-(1-butyl)-4-hydroxy-3-methoxy-2-phenyl-2-cyclobuten-1-one | 122745-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(1-butyl)-4-hydroxy-3-methoxy-2-phenyl-2-cyclobuten-1-one
• 英文别名: 4-butyl-4-hydroxy-3-methoxy-2-phenyl-cyclobut-2-enone；4-butyl-4-hydroxy-3-methoxy-2-phenylcyclobut-2-en-1-one
• CAS: 122745-90-8
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: WSEPITMLSYZIDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(1-butyl)-4-hydroxy-3-methoxy-2-phenyl-2-cyclobuten-1-one 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以91%的产率得到2-(1-butyl)-4-chloro-3-methoxy-4-phenyl-2-cyclobuten-1-one
  参考文献：
  名称：

  Synthesis of p-chlorophenols (and -naphthols) from the thermal rearrangement of 4-chlorocyclobutenones

  摘要：

  A systematic study of the reaction of 4-hydroxycyclobutenones with thionyl chloride is reported. A useful model evolves from this study which allows the prediction of the site of chlorination for unsymmetrical examples. The chlorination is envisaged to involve the corresponding homoaromatic carbocation, and the site of chlorination takes place preferentially at the position substituted with the greater cation-stabilizing substituent. Specifically, this follows the general order of allyl > benzyl > alkyl > propargyl. The 4-chlorocyclobutenones prepared in this study were shown to be useful synthetic precursors to highly substituted chlorophenols and chloronaphthols.

  DOI：

  10.1021/jo00027a057
• 作为产物：
  描述：

  正丁基锂 、 3-methoxy-4-phenylcyclobutenedione 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 4-(1-butyl)-4-hydroxy-3-methoxy-2-phenyl-2-cyclobuten-1-one
  参考文献：
  名称：

  镍催化的具有显着配体作用的α-羟基环烯酮的开环

  摘要：

  本文报道了Ni催化的α-羟基环丁烯酮的开环。开环后的转化过程中观察到了显着的配体效应。PPh3的使用通过烷氧基的迁移导致形成2-呋喃酮2，而在Xantphos的存在下通过氢的迁移生成了2-呋喃酮3，从而提供了一种具有多种功能的2-呋喃酮的发散方法。组。

  DOI：

  10.1039/c7cc03340k

文献信息

• Rearrangement of 4-chloro-4-aryl(or alkenyl)cyclobutenones to p-chlorophenols
  作者：Simon L. Xu、Harold W. Moore

  DOI：10.1021/jo00278a008

  日期：1989.8
• XU, SIMON L.;MOORE, HAROLD W., J. ORG. CHEM., 54,(1989) N7, C. 4024-4026
  作者：XU, SIMON L.、MOORE, HAROLD W.

  DOI：——

  日期：——
• Nickel-catalyzed ring-opening of α-hydroxycyclobutenones with a remarkable ligand effect
  作者：Songsong Gao、Xiangdong Hu

  DOI：10.1039/c7cc03340k

  日期：——

  A Ni-catalyzed ring-opening of α-hydroxycyclobutenones is reported herein. A remarkable ligand effect was observed during transformations following the ring-opening. The employment of PPh3 leads to the formation of 2-furanones 2 through a migration of an alkoxyl group, and 2-furanones 3 were generated through a migration of hydrogen in the presence of Xantphos, affording a divergent approach to 2-furanones

  本文报道了Ni催化的α-羟基环丁烯酮的开环。开环后的转化过程中观察到了显着的配体效应。PPh3的使用通过烷氧基的迁移导致形成2-呋喃酮2，而在Xantphos的存在下通过氢的迁移生成了2-呋喃酮3，从而提供了一种具有多种功能的2-呋喃酮的发散方法。组。
• Synthesis of p-chlorophenols (and -naphthols) from the thermal rearrangement of 4-chlorocyclobutenones
  作者：Simon L. Xu、Harold W. Moore

  DOI：10.1021/jo00027a057

  日期：1992.1

  A systematic study of the reaction of 4-hydroxycyclobutenones with thionyl chloride is reported. A useful model evolves from this study which allows the prediction of the site of chlorination for unsymmetrical examples. The chlorination is envisaged to involve the corresponding homoaromatic carbocation, and the site of chlorination takes place preferentially at the position substituted with the greater cation-stabilizing substituent. Specifically, this follows the general order of allyl > benzyl > alkyl > propargyl. The 4-chlorocyclobutenones prepared in this study were shown to be useful synthetic precursors to highly substituted chlorophenols and chloronaphthols.